Hydrochloric Acid → HCID 136266768, compound

HRID 526108Notes

Reaction equation

HRID 526108 reaction equation
[C:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][C:15]1[CH:16]=[N:17][C:18]([N:21]3[CH2:25][CH2:24][CH:23]([NH:26]C(=O)OC(C)(C)C)[CH2:22]3)=[N:19][CH:20]=1)=[N:11][C:10]([C:34]1[CH:39]=[C:38]([Cl:40])[C:37]([OH:41])=[C:36]([Cl:42])[CH:35]=1)=[CH:9][CH:8]=2)(=[O:3])[CH3:2].[ClH:43]>>[ClH:40].[ClH:43].[ClH:40].[NH2:26][CH:23]1[CH2:24][CH2:25][N:21]([C:18]2[N:19]=[CH:20][C:15]([NH:14][C:13]3[C:12]4[C:7](=[CH:8][CH:9]=[C:10]([C:34]5[CH:39]=[C:38]([Cl:40])[C:37]([OH:41])=[C:36]([Cl:42])[CH:35]=5)[N:11]=4)[N:6]=[CH:5][C:4]=3[C:1](=[O:3])[CH3:2])=[CH:16][N:17]=2)[CH2:22]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 136927337HCID 136927337, compound

Product 1

HCID 136266768HCID 136266768, compoundYield 50%

Procedure

Following general procedure IV-1, tert-butyl 1-{5-[3-acetyl-6-(3,5-dichloro-4-hydroxyphenyl)-1,5-naphthyridin-4-ylamino]pyrimidin-2-yl}pyrrolidin-3-ylcarbamate (123 mg, 0.20 mmol) was reacted with 6 N HCl (2 mL) followed by formation of the trihydrochloride salt to afford the desired product (62 mg, 50%) as a light orange solid: 1H NMR (500 MHz, CD3OD) δ 9.36 (br s, 1H), 8.51-8.35 (m, 3H), 7.51 (br s, 2H), 4.12-3.97 (m, 2H), 3.89-3.84 (m, 1H), 3.80-3.69 (m, 2H), 2.84 (br s, 3H), 2.58-2.48 (m, 1H), 2.28-2.17 (m, 1H); ESI MS m/z 510 [M+H]+; HPLC 95.6% (AUC), tR=9.18 min.

Sources & evidence

ORD record
ord-7381f76c7eef44578c1611b9f163e505
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

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